Episode 850 | How Not to Screw Up When Hiring Your first Developer and More Listener Questions (with Derrick Reimer)

About this episode

How do you onboard a hire onto a codebase you built alone? In this episode, Derrick Reimer joins Rob to tackle four listener questions. They cover hiring and onboarding your first developer as a bootstrapped founder, then move into the temptation to build features just because AI makes them cheap to ship, getting past social anxiety as a founder, and whether it's worth trademarking your product name. Topics we cover: • (3:59) – How do you hire your first developer?   • (5:14) – Qualities to look for in a first developer hire • (13:37) – Onboarding a new hire into your codebase with AI • (16:49) – Reducing hiring risk: pairing, reliability, recruiters • (22:50) – The temptation to build features just because AI makes it cheap • (30:43) – Getting over social anxiety as a founder • (35:25) – Is trademarking your product name worth it? Links from the show: • TinySummit | December 5–7, 2026 · JW Marriott, Cancun • MicroConf US | April 18–20, 2027 · Austin, TX • Partnerships: sponsors@microconf.com • Idea to Traction: Stop Building SaaS Nobody Wants (book wait list) • Rob Walling Newsletter • Remote First Recruiting